US3580966A - Graft copolymers of acrylonitrile onto a linear polyether having quaternised nitrogen atoms - Google Patents

Graft copolymers of acrylonitrile onto a linear polyether having quaternised nitrogen atoms Download PDF

Info

Publication number
US3580966A
US3580966A US787222A US3580966DA US3580966A US 3580966 A US3580966 A US 3580966A US 787222 A US787222 A US 787222A US 3580966D A US3580966D A US 3580966DA US 3580966 A US3580966 A US 3580966A
Authority
US
United States
Prior art keywords
weight
graft
acrylonitrile
parts
nitrogen atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US787222A
Other languages
English (en)
Inventor
Helmut Engelhard
Heinrich Rinkler
Gunther Nischk
Francis Bentz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Application granted granted Critical
Publication of US3580966A publication Critical patent/US3580966A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals

Definitions

  • acrylonitrile graft polymer acrylonitrile and other copolymerisable comonomers are graft-polymerised in the presence of a graft base consisting of a linear polyether having quaternised nitrogen atoms.
  • This invention relates to acrylonitrile graft polymers having a high affinity for acid dyes, and to a process for their production by grafting acrylonitrile, optionally in conjunction with other copolymerisable compounds, on to linear polyethers containing quaternised nitrogen atoms.
  • filaments and yarns produced from acrylonitrile homopolymers and from copolymers of acrylonitrile with neutral comonomers fall short of practical requirements in their aflinity for dyes.
  • acrylonitrile homopolymers and copolymers for acid dyes can be improved by copolymerising acrylonitrile with unsaturated amines, for example vinyl, isopropenyl pyridines, monovinyl alkyl ethers of amino alcohols, acrylic or methacrylic amides, or with acrylic or methacrylic acid glycidyl esters whose epoxy function is subsequently split by amines.
  • unsaturated amines for example vinyl, isopropenyl pyridines, monovinyl alkyl ethers of amino alcohols, acrylic or methacrylic amides, or with acrylic or methacrylic acid glycidyl esters whose epoxy function is subsequently split by amines.
  • copolymers produced in this way are receptive to acid dyes, they frequently have low K-values so that the films and filaments produced from them lack suflicient strength and are only to a limited extent suitable for commercial application.
  • the aforementioned copolymers discolour quite considerably under the effect of heat, both in solution and in solid form.
  • Graft polymers of acrylonitrile on prepolymers such as nylon 6, for example, are also known.
  • a polyether with the following recurring structural unit is obtained, for example, following quaternisation of the polyether of N,N-di-fi-hydroxyethyl-cyclohexylamine with dimethyl sulphate as the graft base:
  • the acrylonitrile is preferably grafted on to the quaternized polyethers in the presence of other copolymerisable monomers, for example acrylic or methacrylic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride or acrylic amides.
  • other copolymerisable monomers for example acrylic or methacrylic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride or acrylic amides.
  • the contribution made by the graft base to the total weight of the reactants to be polymerised amounts to from to 40% by weight, and preferably to from to 20% by weight, based on the unquaternised polyethers.
  • the graft polymers remain in solution so that, if desired, the solutions may either be directly spun or alternatively the polymer'may be precipitated with water and further processed after the acid has been Washed out, as already mentioned.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Graft Or Block Polymers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US787222A 1968-01-04 1968-12-26 Graft copolymers of acrylonitrile onto a linear polyether having quaternised nitrogen atoms Expired - Lifetime US3580966A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0054486 1968-01-04

Publications (1)

Publication Number Publication Date
US3580966A true US3580966A (en) 1971-05-25

Family

ID=7107114

Family Applications (1)

Application Number Title Priority Date Filing Date
US787222A Expired - Lifetime US3580966A (en) 1968-01-04 1968-12-26 Graft copolymers of acrylonitrile onto a linear polyether having quaternised nitrogen atoms

Country Status (9)

Country Link
US (1) US3580966A (un)
AT (1) AT288695B (un)
BE (1) BE726445A (un)
CH (1) CH504484A (un)
DE (1) DE1720771A1 (un)
FR (1) FR2000022A1 (un)
GB (1) GB1206000A (un)
NL (1) NL6900102A (un)
SE (1) SE341273B (un)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873294A (en) * 1988-06-16 1989-10-10 Gaf Corporation Mixture of cationic benzene carboxylate polymers from the reaction of haloacetyl terminated poly(ether-esters) with terminal quaternizing agents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873294A (en) * 1988-06-16 1989-10-10 Gaf Corporation Mixture of cationic benzene carboxylate polymers from the reaction of haloacetyl terminated poly(ether-esters) with terminal quaternizing agents

Also Published As

Publication number Publication date
BE726445A (un) 1969-06-16
CH504484A (de) 1971-03-15
DE1720771A1 (de) 1971-07-15
SE341273B (un) 1971-12-20
NL6900102A (un) 1969-07-08
GB1206000A (en) 1970-09-23
FR2000022A1 (un) 1969-08-29
AT288695B (de) 1971-01-15

Similar Documents

Publication Publication Date Title
US3875202A (en) Sulfates of monoethylenically unsaturated alcohols and the alkenoxylated adducts of said alcohols
US2882262A (en) N-(acryloxyalkyl)- and n-(methacryloxyalkyl)-2-pyrrolidones and polymers thereof
JPS62104802A (ja) 乳化重合用乳化剤
US3478001A (en) Acrylonitrile copolymers with unsaturated sulfobetaines and process for preparing same
US2843562A (en) Cross-linked graft copolymers of vinyl chloride and polyvinyl alcohols and process fo preparing same
US3639357A (en) Process for preparing substituted maleimide polymers
US4255546A (en) Acrylonitrile polymerization in fluorinated hydrocarbons
US3260707A (en) Allyl and methallyl esters of sulfoaliphatic acids, and interpolymers thereof with acrylonitrile
US3580966A (en) Graft copolymers of acrylonitrile onto a linear polyether having quaternised nitrogen atoms
US3539540A (en) N-vinyl-x-alkyl-2-oxazolidinone polymers
US2504074A (en) Interpolymers of acrylamide and methacrylamide
US2897200A (en) New polymerizable vinyl ether quaternary ammonium compounds
US2861051A (en) Cross-linked graft copolymers of acrylonitrile and polyvinyl alcohols and method of preparing same
US3468832A (en) Stable aqueous emulsions
US2834758A (en) Copolymers of n-acrylamido alkyl betaines
US4350801A (en) Process for preparing polymeric oximes
US3206422A (en) Process for the polymerization of unsaturated monomeric organic compounds in aqueous emulsions
US3197447A (en) Polymers and copolymers of acetals of allyl alcohol
US2941969A (en) Copolymer of a quaternary ammonium compound and acrylonitrile, solution thereof, and fiber formed therefrom
US2856386A (en) Allyl carbamate homopolymers and copolymers
US3412077A (en) Polymers of acrylonitrile with olefinically unsaturated semicarbazide
US3557247A (en) Acrylonitrile graft polymers on polyamide substrate
US3520855A (en) Acrylonitrile copolymers
US2794015A (en) Polymers
US3067186A (en) Vinyl chloride polymerisation process